(2E,4E)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

• ChemBase ID: 128997
• Molecular Formular: C12H10O4
• Molecular Mass: 218.2054
• Monoisotopic Mass: 218.0579088
• SMILES: OC(=O)/C=C/C=C/c1ccc2OCOc2c1
• Canonical SMILES: OC(=O)/C=C/C=C/c1ccc2c(c1)OCO2
• InChI: InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1+,4-2+
• InChIKey: RHBGITBPARBDPH-ZPUQHVIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E,4E)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid
• IUPAC Traditional name: piperic acid
• Synonyms: Piperic acid; (2E,4E)-5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoic Acid; (E,E)-Piperonic Acid; Piperinic Acid; Piperonic Acid; (E,E)-Piperic Acid

Database IDs

• CAS Number: 136-72-1
• PubChem SID: 162223299
• PubChem CID: 5370536
• CHEMBL: 332122
• Wikipedia Title: Piperic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.816676
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.60044456
• LogD (pH = 7.4): -0.9681094
• Log P: 2.2865355
• Molar Refractivity: 59.1454 cm^3
• Polarizability: 22.118814 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Greenish Yellow Solid
• Melting Point: 213-215°C
• Boiling Point: decomposes

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - P481530

A metabolite of Piperine.

REFERENCES

• Koul, S., et al.: Bioorg. Med. Chem., 8, 251 (2000)
• Lux, H., et al.: Mol. Biochem. Parasitol., 111, 1 (2000)
• Saraiva, V., et al.: Antimicrob. Agents Chemother., 46, 3472 (2002)